FR2868775B1 - Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable - Google Patents

Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

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Publication number
FR2868775B1
FR2868775B1 FR0403828A FR0403828A FR2868775B1 FR 2868775 B1 FR2868775 B1 FR 2868775B1 FR 0403828 A FR0403828 A FR 0403828A FR 0403828 A FR0403828 A FR 0403828A FR 2868775 B1 FR2868775 B1 FR 2868775B1
Authority
FR
France
Prior art keywords
synthesis
ivabradine
benzazepin
tetrahydro
derivatives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR0403828A
Other languages
English (en)
Other versions
FR2868775A1 (fr
Inventor
Jean Michel Lerestif
Jean Pierre Lecouve
Jean Claude Souvie
Daniel Brigot
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratoires Servier SAS
Original Assignee
Laboratoires Servier SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratoires Servier SAS filed Critical Laboratoires Servier SAS
Priority to FR0403828A priority Critical patent/FR2868775B1/fr
Priority to CA2496712A priority patent/CA2496712C/fr
Priority to SG200500770A priority patent/SG116574A1/en
Priority to US11/060,043 priority patent/US7064200B2/en
Priority to JP2005041810A priority patent/JP4515933B2/ja
Priority to NO20050888A priority patent/NO329861B1/no
Priority to GEAP8647A priority patent/GEP20074136B/en
Priority to MA28112A priority patent/MA27598A1/fr
Priority to CNB2005100542167A priority patent/CN100348585C/zh
Priority to ZA2005/01468A priority patent/ZA200501468B/en
Priority to MYPI20050621A priority patent/MY140904A/en
Priority to NZ538328A priority patent/NZ538328A/en
Priority to AU2005200884A priority patent/AU2005200884B2/en
Priority to BRPI0500590A priority patent/BRPI0500590B8/pt
Priority to UAA200501524A priority patent/UA81773C2/uk
Priority to ARP050100586A priority patent/AR047707A1/es
Priority to KR1020050013860A priority patent/KR100636499B1/ko
Priority to EG2005020086A priority patent/EG25619A/xx
Priority to DK05290383.8T priority patent/DK1614687T3/da
Priority to ES05290383T priority patent/ES2336461T3/es
Priority to DE602005017541T priority patent/DE602005017541D1/de
Priority to PL05290383T priority patent/PL1614687T3/pl
Priority to SI200530864T priority patent/SI1614687T1/sl
Priority to PT05290383T priority patent/PT1614687E/pt
Priority to AT05290383T priority patent/ATE448221T1/de
Priority to PCT/FR2005/000396 priority patent/WO2005111027A1/fr
Priority to RSP-2010/0006A priority patent/RS51232B/sr
Priority to EP05290383A priority patent/EP1614687B1/fr
Priority to EA200500240A priority patent/EA007743B1/ru
Priority to MXPA05003696A priority patent/MXPA05003696A/es
Publication of FR2868775A1 publication Critical patent/FR2868775A1/fr
Priority to HK05111843A priority patent/HK1079777A1/xx
Application granted granted Critical
Publication of FR2868775B1 publication Critical patent/FR2868775B1/fr
Priority to JP2009220529A priority patent/JP5277130B2/ja
Priority to HR20100024T priority patent/HRP20100024T1/hr
Priority to CY20101100053T priority patent/CY1109740T1/el
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
FR0403828A 2004-04-13 2004-04-13 Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable Expired - Fee Related FR2868775B1 (fr)

Priority Applications (34)

Application Number Priority Date Filing Date Title
FR0403828A FR2868775B1 (fr) 2004-04-13 2004-04-13 Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
CA2496712A CA2496712C (fr) 2004-04-13 2005-02-07 Nouveau procede de synthese de derives de la 1,3,4,5-tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
SG200500770A SG116574A1 (en) 2004-04-13 2005-02-15 New process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds, and applicationin the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid.
US11/060,043 US7064200B2 (en) 2004-04-13 2005-02-17 Process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
NZ538328A NZ538328A (en) 2004-04-13 2005-02-18 New process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
GEAP8647A GEP20074136B (en) 2004-04-13 2005-02-18 New process for the synthesis of 1,3,4,5-tetrahydro-2h-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
JP2005041810A JP4515933B2 (ja) 2004-04-13 2005-02-18 １，３，４，５−テトラヒドロ−２ｈ−３−ベンゾアゼピン−２−オン化合物の新規な合成方法、並びにイバブラジン及び薬学的に許容され得る酸とのその付加塩の合成への適用
CNB2005100542167A CN100348585C (zh) 2004-04-13 2005-02-18 1,3,4,5－四氢－2h－3－苯并氮杂䓬－2－酮化合物的合成方法及其应用
ZA2005/01468A ZA200501468B (en) 2004-04-13 2005-02-18 Process for the synthesis of 1,3,4,5-tetrahydro-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
MYPI20050621A MY140904A (en) 2004-04-13 2005-02-18 Process for the synthesis of 1,3,4,5-tetrahydro-2h-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
NO20050888A NO329861B1 (no) 2004-04-13 2005-02-18 Ny fremgangsmate for syntesen av 1,3,4,5-tetrahydro-2H-3-benzazepin-2-onforbindelser, og anvendelse i syntesen av ivabradin og addisjonssalter derav med en farmasoytisk akseptabel syre
AU2005200884A AU2005200884B2 (en) 2004-04-13 2005-02-18 New process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
BRPI0500590A BRPI0500590B8 (pt) 2004-04-13 2005-02-18 processo para a síntese de compostos de 1,3,4,5-tetraidro-2h-3-benzazepin-2-ona, e aplicação na síntese de ivabradina e sais de adição desta com um ácido farmaceuticamente aceitável
UAA200501524A UA81773C2 (uk) 2004-04-13 2005-02-18 Спосіб синтезу сполук 1,3,4,5-тетрагідро-2н-3-бензазепін-2-ону і застосування їх у синтезі івабрадину і його адитивних солей з фармацевтично прийнятною кислотою
ARP050100586A AR047707A1 (es) 2004-04-13 2005-02-18 Un procedimiento de sintesis de compuestos de la 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona, y su aplicacion a la sintesis de la ivabradina y sus sales de adicion con un acido farmaceuticamente aceptable
MA28112A MA27598A1 (fr) 2004-04-13 2005-02-18 Nouveau procede de synthese de derives de la 1,3,4,5-tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
EG2005020086A EG25619A (en) 2004-04-13 2005-02-19 New process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds and application in the synthesis of iv abradine and addition saltsthereof wwith a pharmaceutically acceptable acid
KR1020050013860A KR100636499B1 (ko) 2004-04-13 2005-02-19 1,3,4,5-테트라히드로-2ｈ-3-벤즈아제핀-2-온 화합물의 합성 방법, 및 이바브라딘 및 이의 약제학적으로 허용되는 산과의 부가염의 합성에서의 용도
DK05290383.8T DK1614687T3 (da) 2004-04-13 2005-02-21 Fremgangsmåde til fremstilling af 1,3,4,5-tetrahydro-2H-3-benzazepin-2-onderivater og deres anvendelse ved syntese af ivabradin og farmaceutisk acceptable salte deraf
DE602005017541T DE602005017541D1 (de) 2004-04-13 2005-02-21 Verfahren zur Herstellung von 1,3,4,5-tetrahydro-2H-3-Benzazepin-2-on-Derivaten und dessen Anwendung in der Herstellung von Ivabradin sowie dessen pharmazeutisch verträglichen Salze
PL05290383T PL1614687T3 (pl) 2004-04-13 2005-02-21 Sposób syntezy pochodnych 1,3,4,5-tetrahydro-2H-3-benzazepin-2-onu i ich zastosowania do syntezy iwabradyny oraz jej soli addycyjnych z dopuszczalnym farmaceutycznie kwasem
SI200530864T SI1614687T1 (sl) 2004-04-13 2005-02-21 Nov postopek za sintezo derivatov 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona in njihova uporaba za sintezo ivabradina kot tudi njegovih adicijskih soli s farmacevtsko sprejemljivo kislino
PT05290383T PT1614687E (pt) 2004-04-13 2005-02-21 Novo processo de síntese de derivados da 1,3,4,5- tetrahidro-2h-benzazepin-2-ona, e aplicação à síntese da ivabradina e dos seus sais de adição a um ácido aceitáveis do ponto de vista farmacêutico
AT05290383T ATE448221T1 (de) 2004-04-13 2005-02-21 Verfahren zur herstellung von 1,3,4,5-tetrahydro- 2h-3-benzazepin-2-on-derivaten und dessen anwendung in der herstellung von ivabradin sowie dessen pharmazeutisch verträglichen salze
PCT/FR2005/000396 WO2005111027A1 (fr) 2004-04-13 2005-02-21 Nouveau procede de synthese de derives de la 1,3,4,5­ tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
RSP-2010/0006A RS51232B (sr) 2004-04-13 2005-02-21 Novi postupak sinteze derivata 1,3,4,5-tetrahidro-2h-3benzazepin-2-on-a i primena u sintezi ivabradina i njegovih adicionih soli sa farmaceutski prihvatljivom kiselinom
EP05290383A EP1614687B1 (fr) 2004-04-13 2005-02-21 Nouveau procédé de synthèse de dérivés de la 1,3,4,5-tétrahydro-2H-3-benzazépin-2-one, et application à la synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquement acceptable
EA200500240A EA007743B1 (ru) 2004-04-13 2005-02-21 Способ получения производных 1,3,4,5-тетрагидро-2н-3-бензазепин-2-она
ES05290383T ES2336461T3 (es) 2004-04-13 2005-02-21 Nuevo procedimiento para la sintesis de derivados de 1,3,4,5-tetrahidro-2h-benzacepi-2-ona y su aplicacion a la sintesis de ivabradina y de sus sales de adicion de acido.
MXPA05003696A MXPA05003696A (es) 2004-04-13 2005-04-07 Nuevo proceso para la sintesis de compuestos de 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona, y aplicacion en la sintesis de ivabradina y sales de adicion de la misma con un acido farmaceuticamente aceptable.
HK05111843A HK1079777A1 (en) 2004-04-13 2005-12-22 Process for the synthesis of 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one compounds, and application thereof
JP2009220529A JP5277130B2 (ja) 2004-04-13 2009-09-25 １，３，４，５−テトラヒドロ−２ｈ−３−ベンゾアゼピン−２−オン化合物の新規な合成方法、並びにイバブラジン及び薬学的に許容され得る酸とのその付加塩の合成への適用
HR20100024T HRP20100024T1 (hr) 2004-04-13 2010-01-13 Postupak priprave derivata 1,3,4,5-tetrahidro-2h-3-benzepin-2-ona, njihova primjena u sintezi ivabradina i njihove farmaceutski prihvatljive soli
CY20101100053T CY1109740T1 (el) 2004-04-13 2010-01-19 Νεα μεθοδος συνθεσης παραγωγων της 1,3,4,5 -τετραϋδρο-2η- 3-βενζαζεπιν-2-ονης και εφαρμογη στη συνθεση της ιβαβραδινης και των αλατων προσθηκης της σε ενα φαρμακευτικως αποδεκτο οξυ

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0403828A FR2868775B1 (fr) 2004-04-13 2004-04-13 Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

Publications (2)

Publication Number Publication Date
FR2868775A1 FR2868775A1 (fr) 2005-10-14
FR2868775B1 true FR2868775B1 (fr) 2008-04-11

Family

ID=34941961

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0403828A Expired - Fee Related FR2868775B1 (fr) 2004-04-13 2004-04-13 Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

Country Status (33)

Country Link
US (1) US7064200B2 (fr)
EP (1) EP1614687B1 (fr)
JP (2) JP4515933B2 (fr)
KR (1) KR100636499B1 (fr)
CN (1) CN100348585C (fr)
AR (1) AR047707A1 (fr)
AT (1) ATE448221T1 (fr)
AU (1) AU2005200884B2 (fr)
BR (1) BRPI0500590B8 (fr)
CA (1) CA2496712C (fr)
CY (1) CY1109740T1 (fr)
DE (1) DE602005017541D1 (fr)
DK (1) DK1614687T3 (fr)
EA (1) EA007743B1 (fr)
EG (1) EG25619A (fr)
ES (1) ES2336461T3 (fr)
FR (1) FR2868775B1 (fr)
GE (1) GEP20074136B (fr)
HK (1) HK1079777A1 (fr)
HR (1) HRP20100024T1 (fr)
MA (1) MA27598A1 (fr)
MX (1) MXPA05003696A (fr)
MY (1) MY140904A (fr)
NO (1) NO329861B1 (fr)
NZ (1) NZ538328A (fr)
PL (1) PL1614687T3 (fr)
PT (1) PT1614687E (fr)
RS (1) RS51232B (fr)
SG (1) SG116574A1 (fr)
SI (1) SI1614687T1 (fr)
UA (1) UA81773C2 (fr)
WO (1) WO2005111027A1 (fr)
ZA (1) ZA200501468B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2868775B1 (fr) * 2004-04-13 2008-04-11 Servier Lab Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2868777B1 (fr) * 2004-04-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
GT200500185A (es) * 2004-08-09 2006-04-10 Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos
PT2471780E (pt) 2007-05-30 2015-02-24 Ind Swift Lab Ltd Sais oxalato de ivabradina cristalinos e seus polimorfos
ES2402765T3 (es) 2008-12-22 2013-05-08 Krka, D.D., Novo Mesto Procedimiento de preparación de ivabradina
FR2940287B1 (fr) * 2008-12-24 2010-12-24 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable.
EP2534135A2 (fr) 2010-02-12 2012-12-19 KRKA, D.D., Novo Mesto Nouvelles formes de chlorhydrate d'ivabradine
FR2956401B1 (fr) * 2010-02-17 2012-02-03 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2971507B1 (fr) * 2011-02-14 2013-01-18 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2984320B1 (fr) * 2011-12-20 2013-11-29 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2993561B1 (fr) * 2012-07-17 2014-10-31 Servier Lab Procede de synthese enzymatique de la (7s)-1-(3,4-dimethoxy bicyclo[4.2.0]octa-1,3,5-triene 7-yl) n-methyl methanamine, et application a la synthese de l'ivabradine et de ses sels
FR3003859B1 (fr) * 2013-03-26 2015-03-13 Servier Lab "procede de synthese de derives de la 7,8-dimethoxy-1,3-dihydro-2h-3-benzazepin-2-one et application a la synthese de l'ivabradine"

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3119874A1 (de) * 1981-05-19 1982-12-09 Dr. Karl Thomae Gmbh, 7950 Biberach "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel"
DE3418270A1 (de) * 1984-05-17 1985-11-21 Dr. Karl Thomae Gmbh, 7950 Biberach Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3519735A1 (de) * 1985-06-01 1986-12-04 Dr. Karl Thomae Gmbh, 7950 Biberach Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP0204349A3 (fr) 1985-06-01 1990-01-03 Dr. Karl Thomae GmbH Dérivés d'amines hétéroaromatiques, médicaments les contenant et procédé pour leur préparation
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
FR2868775B1 (fr) * 2004-04-13 2008-04-11 Servier Lab Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2868777B1 (fr) * 2004-04-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

Also Published As

Publication number Publication date
CY1109740T1 (el) 2014-09-10
MA27598A1 (fr) 2005-11-01
BRPI0500590B1 (pt) 2018-10-09
JP4515933B2 (ja) 2010-08-04
US7064200B2 (en) 2006-06-20
PL1614687T3 (pl) 2010-04-30
CA2496712A1 (fr) 2005-10-13
EP1614687A1 (fr) 2006-01-11
RS51232B (sr) 2010-12-31
EG25619A (en) 2012-03-26
CN100348585C (zh) 2007-11-14
NZ538328A (en) 2005-10-28
MY140904A (en) 2010-01-29
JP2010047577A (ja) 2010-03-04
NO20050888L (no) 2005-10-14
AU2005200884B2 (en) 2010-07-15
US20050228178A1 (en) 2005-10-13
SI1614687T1 (sl) 2010-01-29
FR2868775A1 (fr) 2005-10-14
BRPI0500590A (pt) 2005-11-16
HRP20100024T1 (hr) 2010-02-28
CA2496712C (fr) 2010-04-06
EA007743B1 (ru) 2006-12-29
PT1614687E (pt) 2009-12-02
ZA200501468B (en) 2005-11-30
WO2005111027A1 (fr) 2005-11-24
ES2336461T3 (es) 2010-04-13
HK1079777A1 (en) 2006-04-13
SG116574A1 (en) 2005-11-28
KR20060042117A (ko) 2006-05-12
NO20050888D0 (no) 2005-02-18
DE602005017541D1 (de) 2009-12-24
JP5277130B2 (ja) 2013-08-28
EP1614687B1 (fr) 2009-11-11
NO329861B1 (no) 2011-01-17
GEP20074136B (en) 2007-06-25
EA200500240A1 (ru) 2005-10-27
MXPA05003696A (es) 2006-01-24
DK1614687T3 (da) 2010-03-29
AR047707A1 (es) 2006-02-08
JP2005298478A (ja) 2005-10-27
CN1683343A (zh) 2005-10-19
AU2005200884A1 (en) 2005-10-27
BRPI0500590B8 (pt) 2021-05-25
ATE448221T1 (de) 2009-11-15
UA81773C2 (uk) 2008-02-11
KR100636499B1 (ko) 2006-10-18

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